Annisquam River Cruise
See Gloucester Harbor, the Annisquam River, and a quieter side of Cape Ann from the water
Join Cape Ann Cruises aboard the WEJACK for a scenic cruise through Gloucester Harbor and the Annisquam River, one of Cape Ann’s most beautiful and unique waterways.
Departing from our dock in Gloucester Harbor, this trip begins with classic outer harbor views, including Ten Pound Island Lighthouse, Cape Pond Ice, the Greasy Pole, Stage Fort Park, working waterfront scenes, fishing boats, and the historic shoreline that makes Gloucester so special.
From there, we continue through the Blynman Canal, passing under the Blynman Bridge, the Gloucester Railroad Bridge, and the A. Piatt Andrew Bridge before opening into the calm, winding beauty of the Annisquam River.
Along the way, enjoy views of salt marshes, classic New England coastal homes, working boats, sailboats, hidden coves, and the shoreline that gives this part of Gloucester its quiet charm. As we continue north, you’ll see the beautiful waters near Wingaersheek Beach, Annisquam Harbor Light, and views toward Ipswich Bay and the tip of Rockport.
This is a relaxing and scenic way to experience Cape Ann from a different perspective, part harbor cruise, part river tour, part coastal sightseeing adventure.
Grab a drink from our full bar, enjoy the ocean air, and let Captain Jeff and Barbara show you one of Gloucester’s most memorable routes by boat.
Highlights May Include
Gloucester Harbor departure aboard the WEJACK
Ten Pound Island Lighthouse
Cape Pond Ice
The Greasy Pole
Stage Fort Park
Gloucester’s working waterfront
Blynman Canal and the historic Blynman Bridge
Gloucester Railroad Bridge
A. Piatt Andrew Bridge
Scenic Annisquam River views
Salt marshes, boats, and classic New England waterfront homes
Wingaersheek Beach area
Annisquam Harbor Light
Views toward Ipswich Bay and Rockport
Route, timing, and bridge passage may vary based on weather, tide, marine traffic, and bridge openings.
Gloucester Harbor Tour Scenic Points of Interest
Blynman Bridge, Massachusetts 127, Gloucester, MA, USA
Also called the Cut bridge, this draw bridge connects Gloucester Harbor to the Annisquam River splitting the Boulevard in two. We pass by it on this tour without going through it. It is considered a challenging and sometimes dangerous waterway for inexperienced boaters because of the fast currents depending on the tide and other boat traffic.
Cape Pond Ice, Gloucester, Massachusetts
Cape Pond became famous because it was featured in the movie "The Perfect Storm" starring George Clooney and supplies ice to fishing boats.
How to See the Wicked Tuna Boats in Gloucester
Not only is the Wejack a Giant Bluefin tuna built fishing machine, we often see many of the Wicked Tuna Boats on our tours, like Hard Merchandise, Fat Tuna, Hot Tuna, Tuna.com, Wicked Pissah, Pinwheel, Badfish and more. We sometimes see Giant Bluefun Tuna being unloaded from the Tuna boats to the Gloucester Docks. If you want to check out the Wicked Tuna Boats, we highly recommend one of our public tours or private group charters.
We pass by this landmark building on the boat tour located in East Gloucester.
Gloucester Fishermen's Wives Memorial, Gloucester, Massachusetts
This statute depicts a woman and child looking out to sea waiting for their family member to return from fishing.
Fishermen's Memorial Monument, Gloucester, Massachusetts
An Iconic statue with a fisherman and ship's wheel looking out to sea and is also the Gorton's Fish Logo. The names of those lost at sea fishing from Gloucester are carved into the memorial stones surrounding this statue and include the crew members from the Andrea Gail from the Perfect Storm, depicted by George Clooney in the Hollywood Blockbuster movie "The Perfect Storm."
Stage Fort Park and Beach, Gloucester, Massachusetts
We pass the Rocky outcroppings of Stage Fort Park where a Cannon is mounted. This location was once in defense of Gloucester Harbor and Half Moon Beach looks cozy and where one would imagine pirate treasure being hidden.
Experience Gloucester Inner and Outer Harbor.
See beaches, Castles, Mansions, Fishing Boats, Schooners, Lighthouses, Islands, and Marine wildlife.
Ten Pound Lighthouse, Gloucester, Massachusetts
Ten Pound Island and Lighthouse is a former US Coast Guard Seaplane base for chasing down Rumrunners during prohibition. The island marks the boundary between Gloucester Inner and Gloucester Outer Harbor. The tour passes by it on more than one occasion.
What to Bring
Comfortable Shoes, Sunglasses. Sunscreen, Hat. We recommend bringing an extra layer of clothing and a windblock layer. The temperature tends to be cooler on the water, especially around sunset.
What’s Onboard
We have beverages and snacks for purchase and have a toilet (aka head) onboard.